AI Systems Engineer

WebMD LLC; El Segundo (CA); Hybrid; USD 120,000 - 145,000; Full time

Benefits offered by this job

Health Insurance

401(k) Retirement Plan

Paid Time Off

Life and Disability Insurance

Employee Assistance Program (EAP)

Commuter/Transit Benefits

Job summary

WebMD LLC seeks an AI & Systems Engineer to lead the hybrid infrastructure and AI operations for the enterprise. You will manage Windows Server, cloud services, network, security, and AI platforms, ensuring rigorous deployment, hardening, and secure integration with identity controls.

The role blends infrastructure expertise with hands‑on AI engineering, requiring on‑call readiness and collaboration across IT, security, and compliance teams to support HIPAA and data privacy requirements.

Qualifications

• Experience across complete infrastructure stack: network, security, storage, hardware, and OS layer.
• Deep Windows Server administration experience including lifecycle management.
• PowerShell scripting for automation, provisioning, reporting, and sysadmin tasks.
• DNS/DHCP administration including DNSSEC and zone management.
• Experience with NetApp backup tools and DR planning.
• Virtualization expertise with VMware and/or Hyper-V.
• Experience migrating data across cloud, hybrid, and on‑prem environments.
• Experience with Google Workspace, GCP, Office 365, and Azure services.
• Knowledge of IAM tooling and SSO integration (Entra ID, SAML/OIDC).
• Familiarity with AI platform security, governance, and HIPAA/GDPR considerations.

Responsibilities

• Own deployment, configuration, and administration of enterprise AI platforms (Anthropic Claude, Google Gemini) across the organization.
• Architect MCP server infrastructure, registries, and connector governance.
• Enforce data flow, access controls, and security policies for AI systems.
• Design AI hardening, rate limiting, WAF rules, and SIEM integration.
• Maintain runbooks, architecture diagrams, and security assessments.
• Collaborate with legal, compliance, and security teams on HIPAA and privacy obligations.
• Provide cross‑functional IT support and lead enterprise infrastructure initiatives.

Skills

Infrastructure

PowerShell

DNS/DHCP

VMware/Hyper-V

NetApp backups

Cloud platforms

IAM / Entra ID

Azure AD SSO

AI systems engineering

SIEM monitoring

Security governance

Documentation

Tools

VMware

Hyper-V

NetApp

Terraform

Bicep

Google Workspace

GCP

Office 365

Azure

Entra ID / SSO

Job description

WebMD is the most recognized and trusted brand of health information and the leading provider of health information services, serving consumers, physicians, healthcare professionals, employers and health plans through our public and private online portals and WebMD the Magazine. The WebMD Health Network includes WebMD, Medscape, MedicineNet, eMedicine, RxList, theheart.org and Medscape Education. Our consumer portals and mobile health applications provide engaging, relevant and credible health and wellness information, personalized health assessment tools and access to online communities. WebMD is an Equal Opportunity/Affirmative Action employer and does not discriminate on the basis of race, ancestry, color, religion, sex, gender, age, marital status, sexual orientation, gender identity, national origin, medical condition, disability, veterans status, or any other basis protected by law.

Position Overview

The AI & Systems Engineer is a hybrid infrastructure and AI operations role responsible for managing the full enterprise IT stack while also architecting, deploying, securing, and governing AI systems across the organization. This role serves as the primary technical owner for AI platform integrations—including large language models, MCP servers, and connector ecosystems—alongside traditional systems administration responsibilities covering Windows Server, cloud platforms, network infrastructure, and enterprise security. The ideal candidate bridges deep infrastructure expertise with hands-on AI engineering, ensuring AI systems are deployed with rigor, properly hardened, and tightly integrated with existing enterprise identity and security controls.

Position Requirements:

Infrastructure & Systems Administration

• Experience across the complete infrastructure stack: network, security, storage, hardware, and OS layer
• Expertise with Windows Server administration, configuration, upgrades, and lifecycle management
• Deep expertise in PowerShell scripting for automation, provisioning, reporting, and systems management
• Expertise in DNS and DHCP administration, including Windows Server DNS roles, zone management, conditional forwarding, split-brain DNS, and DNSSEC
• Experience with enterprise backup tools including NetApp; building DR environments and failover plans
• Proficiency with virtualization platforms: VMware and/or Hyper-V
• Experience managing and maintaining security patches across server and application estates
• Experience migrating data across cloud, hybrid, and on-premises environments
• Ability to plan, organize, and document complex system maintenance activities; configure systems consistent with institutional policies and procedures
• Comfortable with on-call schedules and response to critical alerts in a timely manner

Cloud & Productivity Platforms

• Experience with Google Workspace administration (user lifecycle, OU management, GAM scripting)
• Experience with Google Cloud Platform (GCP) infrastructure and services
• Experience with Microsoft Office 365 administration including licensing, Exchange Online, and compliance
• Experience with Microsoft Azure including Entra ID (formerly Azure AD), Conditional Access, PIM, and Azure resource management
• Familiarity with setting up and configuring applications with Azure SSO or Google SSO (SAML, OIDC, OAuth 2.0)

AI Systems Engineering & Operations

• Hands-on experience deploying, configuring, and administering large language model (LLM) platforms including Anthropic Claude (claude.ai, Claude API, Claude Code) and Google Gemini across enterprise environments
• Experience architecting and administering MCP (Model Context Protocol) server infrastructure: deploying MCP server instances, configuring tool registries, managing connector ecosystems (Airtable, Atlassian, Google Drive, Gmail, and others), and integrating MCP servers with enterprise identity and access controls
• Ability to design and enforce AI connector governance policies: scope management, permission auditing, credential lifecycle, and connector access reviews
• Experience performing AI platform security assessments covering permission scopes, data flows, output validation pipelines, prompt injection defenses, and HITL (Human-in-the-Loop) controls
• Familiarity with AI hardening principles: model access controls, rate limiting, WAF integration, API gateway configuration, session controls, and kill switch hierarchies for AI systems
• Experience configuring and monitoring SIEM detection rules for AI platform activity and anomaly detection
• Understanding of responsible AI deployment including data residency requirements, privacy-by-design, audit logging, and regulatory alignment (HIPAA, GDPR as applicable)
• Ability to evaluate new AI tools and platforms against enterprise security standards prior to production deployment
• Experience authoring AI systems documentation: architecture diagrams, runbooks, security assessments, and governance policies

Security & Compliance

• Knowledge of applicable data privacy practices, laws, and regulations (HIPAA, SOC 2, GDPR fundamentals)
• Experience with identity and access management (IAM) tooling: Entra ID, Active Directory, SAML/OIDC federation, MFA enforcement, and privileged access management
• Familiarity with network security concepts including firewall policy, VPN administration, WAF configuration, and zero-trust network access models
• Experience with endpoint management using Microsoft Intune or comparable MDM solutions

Certifications & Nice-to-Have

• Certifications in VMware, Hyper-V, MCSE, MCSA, or AWS/Azure Solutions Architect are desirable
• Certifications or coursework in AI/ML platforms, prompt engineering, or responsible AI are a plus
• Experience with infrastructure-as-code tooling (Terraform, Bicep, or comparable) is advantageous
• Familiarity with SIEM platforms (Microsoft Sentinel, Splunk, or similar) for security monitoring
• Experience with acquisition IT integration: user provisioning, mailbox migrations, SSO federation, and directory consolidation

Roles & Responsibilities

Infrastructure Operations

• Provide technical support to corporate business units and support their applications across the enterprise
• Maintain the back-end IT infrastructure estate including servers, storage, UPS, and Hyper-V environments
• Perform Windows Server upgrades, rebuilds, and OS lifecycle management
• Manage and maintain security patches across server infrastructure on a defined cadence
• Migrate data across cloud, hybrid, and on-premises environments with documented rollback plans
• Administer and maintain Windows Server DNS including zone health, record lifecycle, replication, and conditional forwarding configurations
• Build and maintain DR environments, runbooks, and failover/failback plans; participate in DR testing exercises
• Work with or without formal SOPs; author and maintain runbooks and technical documentation as environments evolve
• Proactively learn and document the environments of current and future acquired companies to enable smooth integration
• Serve as a thought leader and architect new IDF/MDF configurations; identify opportunities to scale back or synergize infrastructure across the portfolio
• Be comfortable with on-call schedules and respond to critical alerts in a timely and effective manner

AI Systems Engineering & Governance

• Own the deployment, configuration, and ongoing administration of enterprise AI platforms including Anthropic Claude (claude.ai, Claude API, Claude Code) and Google Gemini; manage platform accounts, access policies, and usage governance
• Architect and manage the enterprise MCP server infrastructure: deploy and maintain MCP server instances, configure tool and connector registries, manage connector lifecycle (onboarding, auditing, deprecation), and enforce data flow and permission policies across connectors
• Integrate AI platforms and MCP servers with enterprise IAM controls (Entra ID / Azure AD SSO, Conditional Access, MFA) to ensure AI system access is governed through standard identity pipelines
• Conduct periodic AI connector and platform security assessments covering permission scopes, credential exposure, data residency, output validation, and prompt injection risk; document findings and drive remediation
• Implement and maintain AI hardening controls: API gateway rate limiting, WAF rules for AI endpoints, session management, kill switch procedures, and anomaly monitoring via SIEM
• Partner with business units to evaluate new AI tools and vendor platforms; perform pre-deployment security reviews and produce architecture documentation before production rollout
• Maintain comprehensive documentation for all AI systems: architecture diagrams, security assessment reports, connector governance policies, and operational runbooks
• Stay current with developments in enterprise AI platforms, MCP ecosystem tooling, and AI security best practices; translate emerging capabilities into actionable infrastructure improvements
• Collaborate with legal, compliance, and security teams to ensure AI platform usage aligns with HIPAA, data privacy obligations, and organizational policy

Collaboration & Stakeholder Engagement

• Establish strong working relationships with corporate business units, the Operations team, IT leadership, and direct manager
• Work cross-functionally to coordinate large-scale infrastructure efforts, migrations, and AI platform rollouts
• Represent IT infrastructure and AI operations as a subject-matter expert in cross-team planning and architecture discussions
• Communicate project status, risks, and decisions clearly to both technical and non-technical stakeholders

Salary range: $120,000 - $145,000

Bonus Eligible: This position is also eligible for a discretionary company bonus, based upon business results.

Benefits: Employees in this position are eligible to participate in the company sponsored benefit programs, including the following within the first 12 months of employment:

• Health Insurance (medical, dental, and vision coverage)
• Paid Time Off (including vacation, sick leave, and flexible holiday days)
• 401(k) Retirement Plan with employer matching
• Life and Disability Insurance
• Employee Assistance Program (EAP)
• Commuter and/or Transit Benefits (if applicable)

Eligibility for specific benefits may vary based on job classification, schedule (e.g., full-time vs. part‑time), work location and length of employment.